WO2008154612A1 - Azeotropic and azeotrope-like compositions of e-1,1,1,4,4,4-hexafluoro-2-butene - Google Patents
Azeotropic and azeotrope-like compositions of e-1,1,1,4,4,4-hexafluoro-2-butene Download PDFInfo
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- WO2008154612A1 WO2008154612A1 PCT/US2008/066621 US2008066621W WO2008154612A1 WO 2008154612 A1 WO2008154612 A1 WO 2008154612A1 US 2008066621 W US2008066621 W US 2008066621W WO 2008154612 A1 WO2008154612 A1 WO 2008154612A1
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- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
- C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
- C08J9/143—Halogen containing compounds
- C08J9/144—Halogen containing compounds containing carbon, halogen and hydrogen only
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- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D1/00—Fire-extinguishing compositions; Use of chemical substances in extinguishing fires
- A62D1/0028—Liquid extinguishing substances
- A62D1/0057—Polyhaloalkanes
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- A—HUMAN NECESSITIES
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- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D1/00—Fire-extinguishing compositions; Use of chemical substances in extinguishing fires
- A62D1/0071—Foams
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- A—HUMAN NECESSITIES
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- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
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- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
- C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
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- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
- C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
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- C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
- C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
- C08J9/143—Halogen containing compounds
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- C08J9/145—Halogen containing compounds containing carbon, halogen and hydrogen only only chlorine as halogen atoms
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- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
- C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
- C08J9/143—Halogen containing compounds
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- C08J9/146—Halogen containing compounds containing carbon, halogen and hydrogen only only fluorine as halogen atoms
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- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
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- C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
- C08J9/149—Mixtures of blowing agents covered by more than one of the groups C08J9/141 - C08J9/143
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/30—Materials not provided for elsewhere for aerosols
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
- C09K5/041—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems
- C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
- C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
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- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5036—Azeotropic mixtures containing halogenated solvents
- C11D7/504—Azeotropic mixtures containing halogenated solvents all solvents being halogenated hydrocarbons
- C11D7/505—Mixtures of (hydro)fluorocarbons
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- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5036—Azeotropic mixtures containing halogenated solvents
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- C11D7/5054—Mixtures of (hydro)chlorofluorocarbons and (hydro) fluorocarbons
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- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
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- C11D7/50—Solvents
- C11D7/5036—Azeotropic mixtures containing halogenated solvents
- C11D7/5068—Mixtures of halogenated and non-halogenated solvents
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- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
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- C11D7/5068—Mixtures of halogenated and non-halogenated solvents
- C11D7/5077—Mixtures of only oxygen-containing solvents
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
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- C11D7/5086—Mixtures of only oxygen-containing solvents the oxygen-containing solvents being different from alcohols, e.g. mixtures of water and ethers
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- C08J2203/02—CO2-releasing, e.g. NaHCO3 and citric acid
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- C08J2203/00—Foams characterized by the expanding agent
- C08J2203/14—Saturated hydrocarbons, e.g. butane; Unspecified hydrocarbons
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- C08J2207/00—Foams characterised by their intended use
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- C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
- C09K2205/10—Components
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- C09K2205/126—Unsaturated fluorinated hydrocarbons
Definitions
- the present disclosure relates to azeotropic or azeotrope-like compositions of E-1,1,1,4,4,4-hexafluoro-2-butene.
- CFCs chlorofluorocarbons
- HCFCs hydrochlorofluorocarbons
- HFCs hydrofluorocarbons
- the HFCs do not contribute to the destruction of stratospheric ozone, but are of concern due to their contribution to the "greenhouse effect", i.e., they contribute to global warming. As a result of their contribution to global warming, the HFCs have come under scrutiny, and their widespread use may also be limited in the future. Thus, there is a need for compositions that do not contribute to the destruction of stratospheric ozone and also have low global warming potentials (GWPs).
- This application includes seven different types of azeotropic or azeotrope-like mixtures.
- This disclosure provides a composition consisting essentially of (a) E-FC-1336mzz and (b) methyl formate; wherein the methyl formate is present in an effective amount to form an azeotrope-like mixture with E- FC-1336mzz.
- This disclosure also provides a composition consisting essentially of (a) E-FC-1336mzz and (b) n-pentane; wherein the n-pentane is present in an effective amount to form an azeotropic or azeotrope-like mixture with E-FC-1336mzz.
- This disclosure also provides a composition consisting essentially of (a) E-FC-1336mzz and (b) 2-methylbutane (isopentane); wherein the isopentane is present in an effective amount to form an azeotropic or azeotrope-like mixture with E-FC-1336mzz.
- This disclosure also provides a composition consisting essentially of (a) E-FC-1336mzz and (b) trans-1,2-dichloroethylene; wherein the trans- 1,2-dichloroethylene is present in an effective amount to form an azeotrope-like mixture with E-FC-1336mzz.
- This disclosure also provides a composition consisting essentially of (a) E-FC-1336mzz and (b) 1,1,1,3,3-pentafluoropropane (CF 3 CH 2 CF 2 H, HFC-245fa); wherein the HFC-245fa is present in an effective amount to form an azeotrope-like mixture with E-FC- 1336mzz.
- the disclosure also provides a composition consisting essentially of (a) E-FC-1336mzz and (b) n-butane; wherein the n-butane is present in an effective amount to form an azeotropic or azeotrope-like mixture with E- FC-1336mzz.
- the disclosure also provides a composition consisting essentially of (a) E-FC-1336mzz and (b) 2-methyl-propane (isobutane); wherein the 2- methylpropane is present in an effective amount to form an azeotropic or azeotrope-like mixture with E-FC-1336mzz.
- FIG. 1 - FIG. 1 is a graphical representation of azeotrope-like compositions consisting essentially of E-FC-1336mzz and methyl formate at a temperature of about 20.0 °C.
- FIG. 2 - FIG. 2 is a graphical representation of an azeotrope and azeotrope-like compositions consisting essentially of E-FC-1336mzz and n-pentane at a temperature of about 20.0 °C.
- FIG. 3 - FIG. 3 is a graphical representation of an azeotrope and azeotrope-like compositions consisting essentially of E-FC-1336mzz and isopentane at a temperature of about 20.0 °C.
- FIG.4 - FIG.4 is a graphical representation of azeotrope-like compositions consisting essentially of E-FC-1336mzz and trans- 1,2- dichloroethylene at a temperature of about 20.0 °C.
- FIG. 5 - FIG. 5 is a graphical representation of azeotrope-like compositions consisting essentially of E-FC-1336mzz and HFC-245fa at a temperature of about 20.0 °C.
- FIG. 6 - FIG. 6 is a graphical representation of an azeotrope and azeotrope-like compositions consisting essentially of E-FC-1336mzz and n-butane at a temperature of about 20.0 °C.
- FIG. 7 - FIG. 7 is a graphical representation of an azeotrope and azeotrope-like compositions consisting essentially of E-FC-1336mzz and isobutane at a temperature of about 20.0 °C.
- a pure single component or an azeotropic or azeotrope-like mixture is desirable.
- a blowing agent composition also known as foam expansion agents or foam expansion compositions
- the composition may change during its application in the foam forming process. Such change in composition could detrimentally affect processing or cause poor performance in the application.
- a refrigerant is often lost during operation through leaks in shaft seals, hose connections, soldered joints and broken lines. In addition, the refrigerant may be released to the atmosphere during maintenance procedures on refrigeration equipment.
- the refrigerant is not a pure single component or an azeotropic or azeotrope-like composition
- the refrigerant composition may change when leaked or discharged to the atmosphere from the refrigeration equipment.
- the change in refrigerant composition may cause the refrigerant to become flammable or to have poor refrigeration performance.
- FC-1336mzz may exist as one of two configurational isomers, E or Z.
- FC-1336mzz as used herein refers to the isomers, Z-FC-1336mzz or E-FC-1336mzz, as well as any combinations or mixtures of such isomers.
- the terms “comprises,” “comprising,” “includes,” “including,” “has,” “having” or any other variation thereof, are intended to cover a non-exclusive inclusion.
- a process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus.
- “or” refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).
- E-FC-1336mzz is a known compound, and its preparation method has been disclosed, for example, in Dawoodi, et. al., Journal of the Chemical Society, Chemical Communications (1982), (12), 696-8, hereby incorporated by reference in its entirety.
- compositions comprising E-FC-1336mzz.
- the composition consists essentially of (a) E-FC-1336mzz and (b) methyl formate; wherein the methyl formate is present in an effective amount to form an azeotrope-like mixture with E-FC- 1336mzz.
- the composition consists essentially of (a) E-FC-1336mzz and (b) n-pentane; wherein the n-pentane is present in an effective amount to form an azeotropic or azeotrope-like mixture with E-FC-1336mzz.
- the composition consists essentially of (a) E-FC-1336mzz and (b) isopentane; wherein the isopentane is present in an effective amount to form an azeotropic or azeotrope-like mixture with E-FC-1336mzz.
- the composition consists essentially of (a) E-FC-1336mzz and (b) trans- 1,2-dichloroethylene; wherein the trans-1,2-dichloroethylene is present in an effective amount to form an azeotrope-like mixture with E-FC- 1336mzz.
- the composition consists essentially of (a) E-FC-1336mzz and (b) HFC-245fa; wherein the HFC- 245fa is present in an effective amount to form an azeotrope-like mixture with E-FC-1336mzz.
- the composition consists essentially of (a) E-FC-1336mzz and (b) n-butane; wherein the n-butane is present in an effective amount to form an azeotropic or azeotrope-like mixture with E-FC-1336mzz.
- the composition consists essentially of (a) E-FC-1336mzz and (b) 2-methyl-propane (isobutane); wherein the 2-methylpropane is present in an effective amount to form an azeotropic or azeotrope-like mixture with E-FC-1336mzz.
- effective amount is meant an amount, which, when combined with E-FC-1336mzz, results in the formation of an azeotropic or azeotrope-like mixture.
- This definition includes the amounts of each component, which amounts may vary depending on the pressure applied to the composition so long as the azeotropic or azeotrope-like compositions continue to exist at the different pressures, but with possible different boiling points. Therefore, effective amount includes the amounts, such as may be expressed in weight or mole percentages, of each component of the compositions of the instant invention which form azeotropic or azeotrope-like compositions at temperatures or pressures other than as described herein.
- an azeotropic composition is an admixture of two or more different components which, when in liquid form under a given pressure, will boil at a substantially constant temperature, which temperature may be higher or lower than the boiling temperatures of the individual components, and which will provide a vapor composition essentially identical to the overall liquid composition undergoing boiling, (see, e.g., M. F. Doherty and M.F. Malone, Conceptual Design of
- an azeotropic composition may be defined in terms of the unique relationship that exists among the components or in terms of the compositional ranges of the components or in terms of exact weight percentages of each component of the composition characterized by a fixed boiling point at a specified pressure.
- an azeotrope-like composition means a composition that behaves like an azeotropic composition (i.e., has constant boiling characteristics or a tendency not to fractionate upon boiling or evaporation). Hence, during boiling or evaporation, the vapor and liquid compositions, if they change at all, change only to a minimal or negligible extent. This is to be contrasted with non-azeotrope-like compositions in which during boiling or evaporation, the vapor and liquid compositions change to a substantial degree.
- compositions with a difference in dew point pressure and bubble point pressure of less than or equal to 5 percent (based upon the bubble point pressure) is considered to be azeotrope-like.
- Relative volatility is the ratio of the volatility of component 1 to the volatility of component 2.
- the ratio of the mole fraction of a component in vapor to that in liquid is the volatility of the component.
- a method known as the PTx method can be used. In this procedure, the total absolute pressure in a cell of known volume is measured at a constant temperature for various compositions of the two compounds.
- Use of the PTx Method is described in detail in "Phase Equilibrium in Process Design", Wiley-lnterscience Publisher, 1970, written by Harold R. Null, on pages 124 to 126; hereby incorporated by reference. These measurements can be converted into equilibrium vapor and liquid compositions in the PTx cell by using an activity coefficient equation model, such as the Non-Random, Two-Liquid (NRTL) equation, to represent liquid phase nonidealities.
- an activity coefficient equation such as the NRTL equation is described in detail in "The Properties of Gases and Liquids," 4th edition, published by McGraw Hill, written by
- FIG. 2 The vapor pressure measured versus the compositions in the PTx cell for E-FC-1336mzz/n-pentane mixture is shown in FIG. 2, which graphically illustrates the formation of an azeotropic and azeotrope-like composition consisting essentially of E-FC-1336mzz and n-pentane as indicated by a mixture of about 84.6 mole % E-1,1,1,4,4,4-hexafluoro-2- butene and 15.4 mole % n-pentane having the highest pressure over the range of compositions at this temperature.
- E-FC-1336mzz and n-pentane form azeotropic compositions ranging from about 82.2 mole percent to about 95.3 mole percent E-FC-1336mzz and from about 17.8 mole percent to about 4.7 mole percent n-pentane (which form azeotropic compositions boiling at a temperature of from about -20 °C to about 80 °C and at a pressure of from about 4.5 psia (31 kPa) to about 139 psia (951 kPa)).
- Some embodiments of azeotropic compositions are listed in Table 1.
- azeotrope-like compositions containing E-FC-1336mzz and n- pentane may also be formed. Such azeotrope-like compositions exist around azeotropic compositions. Some embodiments of azeotrope-like compositions are listed in Table 2. Additional embodiments of azeotrope- like compositions are listed in Table 3.
- FIG. 1 illustrates graphically the formation of azeotrope-like compositions consisting essentially of E-1,1,1,4,4,4-hexafluoro-2-butene and methyl formate at 20.0 °C, as indicated by mixtures of about 83 mole % to about 99 mole % E-1,1,1,4,4,4-hexafluoro-2-butene and about 17 to about 1 mole % methyl formate.
- azeotrope-like compositions Some embodiments of azeotrope-like compositions are listed in Table 4. Additional embodiments of azeotrope-like compositions are listed in Table 5.
- E-FC- 1336mzz and isopentane form azeotropic compositions ranging from about 75.1 mole percent to about 95.4 mole percent E-FC-1336mzz and from about 24.9 mole percent to about 4.6 mole percent isopentane (which form azeotropic compositions boiling at a temperature of from about -40 °C to about 100 °C and at a pressure of from about 1.6 psia (11 kPa) to about 218 psia (1503 kPa)).
- Some embodiments of azeotropic compositions are listed in Table 6.
- azeotrope-like compositions containing E-FC-1336mzz and isopentane may also be formed. Such azeotrope-like compositions exist around azeotropic compositions. Some embodiments of azeotrope- like compositions are listed in Table 7. Additional embodiments of azeotrope-like compositions are listed in Table 8.
- azeotrope-like compositions Some embodiments of azeotrope-like compositions are listed in Table 9. Additional embodiments of azeotrope-like compositions are listed in Table 10. Table 9. Azeotrope-like Compositions
- the total absolute pressure in a PTx cell of known volume was measured at constant temperature for various binary compositions. These measurements were then reduced to equilibrium vapor and liquid compositions in the cell using the NRTL equation.
- FIG. 5 The vapor pressure measured versus the compositions in the PTx cell for E-FC-1336mzz/ HFC-245fa mixture is shown in FIG. 5, which illustrates graphically the formation of azeotrope-like compositions of E-
- azeotrope-like compositions Some embodiments of azeotrope-like compositions are listed in Table 11. Additional embodiments of azeotrope-like compositions are listed in Table 12. Table 11. Azeotrope-like Compositions
- FIG. 6 illustrates graphically the formation of an azeotropic composition of E- 1,1,1,4,4,4-hexafiuoro-2-butene and cyclopentane at 20.0 °C, as indicated by a mixture of about 38.1 mole % E- 1,1,1,4,4,4-hexafluoro-2-butene and 61.9 mole % n-butane having the highest pressure over the range of compositions at this temperature.
- E-FC- 1336mzz and n-butane form azeotropic compositions ranging from about 29.5 mole percent to about 47.2 mole percent E-FC-1336mzz and from about 70.5 mole percent to about 52.8 mole percent n-butane (which form azeotropic compositions boiling at a temperature of from about -40 °C to about 100 °C and at a pressure of from about 3.0 psia (21 kPa) to about 277 psia (1910 kPa)).
- Some embodiments of azeotropic compositions are listed in Table 13.
- azeotrope-like compositions containing E-FC-1336mzz and n-butane may also be formed. Such azeotrope-like compositions exist around azeotropic compositions. Some embodiments of azeotrope- like compositions are listed in Table 14. Additional embodiments of azeotrope-like compositions are listed in Table 15.
- FIG. 7 illustrates graphically the formation of an azeotropic composition of E- 1,1 ,1,4,4-hexafluoro-2-butene and cyclopentane at 20.0 °C, as indicated by a mixture of about 24.9 mole % E- 1,1,1,4,4,4-hexafluoro-2-butene and 75.1 mole % isobutane having the highest pressure over the range of compositions at this temperature.
- E-FC- 1336mzz and isobutane form azeotropic compositions ranging from about 19.4 mole percent to about 32.4 mole percent E-FC-1336mzz and from about 80.6 mole percent to about 67.6 mole percent isobutane (which form azeotropic compositions boiling at a temperature of from about -40 °C to about 80 °C and at a pressure of from about 4.5 psia (31 kPa) to about 218 psia (1503 kPa)).
- Some embodiments of azeotropic compositions are listed in Table 16.
- azeotrope-like compositions containing E-FC-1336mzz and isobutane may also be formed. Such azeotrope-like compositions exist around azeotropic compositions. Some embodiments of azeotrope- like compositions are listed in Table 17. Additional embodiments of azeotrope-like compositions are listed in Table 18.
- the azeotropic or azeotrope-like compositions of the present invention can be prepared by any convenient method including mixing or combining the desired amounts.
- an azeotropic or azeotrope-like composition can be prepared by weighing the desired component amounts and thereafter combining them in an appropriate container.
- the azeotropic or azeotrope-like compositions of the present invention can be used in a wide range of applications, including their use as aerosol propellants, refrigerants, solvents, cleaning agents, blowing agents (foam expansion agents) for thermoplastic and thermoset foams, heat transfer media, gaseous dielectrics, fire extinguishing and suppression agents, power cycle working fluids, polymerization media, particulate removal fluids, carrier fluids, buffing abrasive agents, and displacement drying agents.
- One embodiment of this invention provides a process for preparing a thermoplastic or thermoset foam.
- the process comprises using an azeotropic or azeotrope-like composition as a blowing agent, wherein said azeotropic or azeotrope-like composition consists essentially of E- 1,1,1,4,4,4-hexafluoro-2-butene and a component selected from the group consisting of methyl formate, n-pentane, 2-methylbutane, , trans-1,2- dichloroethylene, 1,1,1,3,3-pentafiuoropropane, n-butane and isobutane.
- Another embodiment of this invention provides a process for producing refrigeration.
- the process comprises condensing an azeotropic or azeotrope-like composition and thereafter evaporating said azeotropic or azeotrope-like composition in the vicinity of the body to be cooled, wherein said azeotropic or azeotrope-like composition consists essentially of E-1,1,1,4,4,4-hexafluoro-2-butene and a component selected from the group consisting of methyl formate, n-pentane, 2-methylbutane, , trans- 1,2-dichloroethylene, 1,1,1,3,3-pentafluoropropane, n-butane and isobutane.
- Another embodiment of this invention provides a process using an azeotropic or azeotrope-like composition as a solvent, wherein said azeotropic or azeotrope-like composition consists essentially of E- 1,1,1,4,4,4-hexafluoro-2-butene and a component selected from the group consisting of methyl formate, n-pentane, 2-methylbutane, , trans- 1,2- dichloroethylene, 1,1,1,3,3-pentafluoropropane, n-butane and isobutane.
- Another embodiment of this invention provides a process for producing an aerosol product.
- the process comprises using an azeotropic or azeotrope-like composition as a propellant, wherein said azeotropic or azeotrope-like composition consists essentially of E-1,1,1,4,4,4- hexafluoro-2-butene and a component selected from the group consisting of methyl formate, n-pentane, 2-methylbutane, , trans-1,2- dichloroethylene, 1,1,1,3,3-pentafluoropropane, n-butane and isobutane.
- Another embodiment of this invention provides a process using an azeotropic or azeotrope-like composition as a heat transfer media, wherein said azeotropic or azeotrope-like composition consists essentially of E-1,1,1,4,4,4-hexafluoro-2-butene and a component selected from the group consisting of methyl formate, n-pentane, 2-methylbutane, 1 , trans- 1,2-dichloroethylene, 1,1,1,3,3-pentafluoropropane, n-butane and isobutane.
- Another embodiment of this invention provides a process for extinguishing or suppressing a fire.
- the process comprises using an azeotropic or azeotrope-like composition as a fire extinguishing or suppression agent, wherein said azeotropic or azeotrope-like composition consists essentially of E-1,1,1,4,4,4-hexafluoro-2-butene and a component selected from the group consisting of methyl formate, n-pentane, 2- methylbutane, trans-1,2-dichloroethylene, 1,1,1,3,3-pentafluoropropane, n- butane and isobutane.
- Another embodiment of this invention provides a process using an azeotropic or azeotrope-like composition as dielectrics, wherein said azeotropic or azeotrope-like composition consists essentially of E- 1,1,1,4,4,4-hexafluoro-2-butene and a component selected from the group consisting of methyl formate, n-pentane, 2-methylbutane, , trans-1,2- dichloroethylene, 1,1,1,3,3-pentafluoropropane, n-butane and isobutane.
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Abstract
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Priority Applications (17)
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BR122018074418-9A BR122018074418B1 (en) | 2007-06-12 | 2008-06-12 | COMPOSITION AND PROCESS TO PRODUCE COOLING |
EP08770760.0A EP2152833B1 (en) | 2007-06-12 | 2008-06-12 | Azeotropic and azeotrope-like compositions of e-1,1,1,4,4,4-hexafluoro-2-butene |
BR122018074411-1A BR122018074411B1 (en) | 2007-06-12 | 2008-06-12 | COMPOSITION AND PROCESS TO PRODUCE COOLING |
AU2008261695A AU2008261695B2 (en) | 2007-06-12 | 2008-06-12 | Azeotropic and azeotrope-like compositions of E-1,1,1,4,4,4-hexafluoro-2-butene |
MX2009013465A MX2009013465A (en) | 2007-06-12 | 2008-06-12 | Azeotropic and azeotrope-like compositions of e-1,1,1,4,4,4-hexafluoro-2-butene. |
BR122018074416-2A BR122018074416B1 (en) | 2007-06-12 | 2008-06-12 | COMPOSITION AND PROCESS TO PRODUCE COOLING |
BR122018074413-8A BR122018074413B1 (en) | 2007-06-12 | 2008-06-12 | COMPOSITION AND PROCESS TO PRODUCE COOLING |
CN201910999572.8A CN110643328B (en) | 2007-06-12 | 2008-06-12 | Azeotropic and azeotrope-like compositions of E-1,1,1,4,4, 4-hexafluoro-2-butene |
BRPI0809736A BRPI0809736B8 (en) | 2007-06-12 | 2008-06-12 | composition and process to produce refrigeration |
CA2684290A CA2684290C (en) | 2007-06-12 | 2008-06-12 | Azeotropic and azeotrope-like compositions of e-1,1,1,4,4,4-hexafluoro-2-butene |
BR122018074407-3A BR122018074407B1 (en) | 2007-06-12 | 2008-06-12 | COMPOSITION AND PROCESS TO PRODUCE COOLING |
CN200880019944.6A CN101679841B (en) | 2007-06-12 | 2008-06-12 | Azeotropic and azeotrope-like compositions of e-1,1,1,4,4,4-hexafluoro-2-butene |
KR1020107000495A KR101434710B1 (en) | 2007-06-12 | 2008-06-12 | Azeotropic and azeotrope-like compositions of e-1,1,1,4,4,4-hexafluoro-2-butene |
ES08770760.0T ES2509882T3 (en) | 2007-06-12 | 2008-06-12 | Azeotropic and azeotrope-like compositions of E-1,1,1,4,4,4-hexafluoro-2-butene |
US12/598,038 US7972525B2 (en) | 2007-06-06 | 2008-06-12 | Azeotropic and azeotrope-like compositions of E-1,1,1,4,4,4-hexafluoro-2-butene |
JP2010512334A JP5460586B2 (en) | 2007-06-12 | 2008-06-12 | Azeotropic and azeotrope-like compositions of E-1,1,1,4,4,4-hexafluoro-2-butene |
US13/112,043 US8262924B2 (en) | 2007-06-12 | 2011-05-20 | Azeotropic and azeotrope-like compositions of E-1,1,1,4,4,4-hexafluoro-2-butene |
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US12/598,038 A-371-Of-International US7972525B2 (en) | 2007-06-06 | 2008-06-12 | Azeotropic and azeotrope-like compositions of E-1,1,1,4,4,4-hexafluoro-2-butene |
US13/112,043 Continuation US8262924B2 (en) | 2007-06-12 | 2011-05-20 | Azeotropic and azeotrope-like compositions of E-1,1,1,4,4,4-hexafluoro-2-butene |
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EP (1) | EP2152833B1 (en) |
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CN (7) | CN101679841B (en) |
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BR (6) | BR122018074413B1 (en) |
CA (1) | CA2684290C (en) |
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CA3148796A1 (en) * | 2019-10-10 | 2021-04-15 | The Chemours Company Fc, Llc | Azeotrope and azeotrope-like compositions comprising neopentane and isomers of hfo-1336mzz |
CN112795372B (en) * | 2021-04-08 | 2021-07-16 | 泉州宇极新材料科技有限公司 | Azeotropic or azeotrope-like compositions comprising chain-like and cyclic fluorides |
CN113789155B (en) * | 2021-09-16 | 2022-06-28 | 珠海格力电器股份有限公司 | Mixed refrigerant and air conditioning system |
TW202346449A (en) * | 2022-04-22 | 2023-12-01 | 美商科慕Fc有限責任公司 | Fluorobutene compositions comprising e-1,1,1,4,4,4-hexafluoro-2-butene and uses thereof |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05179043A (en) * | 1991-11-18 | 1993-07-20 | Daikin Ind Ltd | Blowing agent comprising fluorobutene and production of plastic foam |
EP0558763A1 (en) * | 1991-09-25 | 1993-09-08 | Daikin Industries, Ltd. | Refrigerant and refrigerator |
US20070007488A1 (en) * | 2003-10-27 | 2007-01-11 | Honeywell International, Inc. | Compositions containing fluorine substituted olefins |
US20070096051A1 (en) * | 2005-11-01 | 2007-05-03 | Nappa Mario J | Fire extinguishing and fire suppression compositions comprising unsaturated fluorocarbons |
US20070100011A1 (en) * | 2005-11-01 | 2007-05-03 | Creazzo Joseph A | Blowing agents for forming foam comprising unsaturated fluorocarbons |
Family Cites Families (63)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL251879A (en) | 1959-05-22 | 1900-01-01 | ||
DE1122697B (en) | 1960-05-06 | 1962-01-25 | Bayer Ag | Process for the production of foams based on isocyanate |
US3884828A (en) | 1970-10-15 | 1975-05-20 | Dow Corning | Propellants and refrigerants based on trifluoropropene |
US3723318A (en) | 1971-11-26 | 1973-03-27 | Dow Corning | Propellants and refrigerants based on trifluoropropene |
NL179914C (en) | 1975-11-04 | 1986-12-01 | Dow Chemical Co | METHOD FOR MANUFACTURING A FOAM ARTICLE FROM A THERMOPLASTIC ALKENYL AROMATIC RESIN BY EXTRUSION. |
US4394491A (en) | 1980-10-08 | 1983-07-19 | The Dow Chemical Company | Addition polymerizable adduct of a polymeric monoahl and an unsaturated isocyanate |
FR2523956A1 (en) | 1982-03-26 | 1983-09-30 | Ugine Kuhlmann | BIS- (PERFLUOROALKYL) -1,2-ETHENES BRANCHED, THEIR PREPARATION AND THEIR USE AS OXYGEN TRANSPORTERS ELECTROMECHANICAL CONVERTER |
GB8516826D0 (en) | 1985-07-03 | 1985-08-07 | Dow Chemical Nederland | Precursor compositions of nitrogen-containing polyols |
US4704410A (en) | 1986-06-30 | 1987-11-03 | The Dow Chemical Company | Molded rigid polyurethane foams prepared from aminoalkylpiperazine-initiated polyols |
DD253431A1 (en) | 1986-10-21 | 1988-01-20 | Petrolchemisches Kombinat | METHOD FOR PRODUCING INSULATING OILS |
EP0350316B1 (en) | 1988-07-08 | 1997-05-02 | Rhone-Poulenc Chimie | Cleaning and drying of electronic assemblies |
US4945119A (en) | 1989-05-10 | 1990-07-31 | The Dow Chemical Company | Foaming system for rigid urethane and isocyanurate foams |
FR2658532B1 (en) * | 1990-02-20 | 1992-05-15 | Atochem | APPLICATION OF (PERFLUOROALKYL) -ETHYLENES AS CLEANING OR DRYING AGENTS, AND COMPOSITIONS FOR USE THEREOF. |
US5037572A (en) | 1990-10-03 | 1991-08-06 | E. I. Du Pont De Nemours And Company | Ternary azeotropic compositions of n-perfluorobutylethylene and trans-1,2-dichloroethylene with methanol or ethanol or isopropanol |
JPH04277803A (en) * | 1991-03-05 | 1992-10-02 | Fujitsu Ten Ltd | Program controller |
US5204159A (en) | 1991-03-29 | 1993-04-20 | Tan Domingo K L | Deformable, slip-free, anti-skid pads for snow and ice |
US5164419A (en) | 1991-05-20 | 1992-11-17 | E. I. Du Pont De Nemours And Company | Blowing agent and process for preparing polyurethane foam |
US5194170A (en) * | 1992-04-02 | 1993-03-16 | E. I. Du Pont De Nemours And Company | Binary azeotropic compositions of 1,1,2,2,3,3,4,4-octafluorobutane and either tran-1,2-dichloroethylene, cis 1,2-dichloroethylene, or 1-1 dichloroethane |
US5332761A (en) | 1992-06-09 | 1994-07-26 | The Dow Chemical Company | Flexible bimodal foam structures |
DE69320059T2 (en) * | 1992-11-20 | 1999-01-14 | Daikin Industries, Ltd., Osaka | METHOD FOR PRODUCING 1,1,1,4,4,4-HEXAFLUORO-2-BUTEN AND 1,1,1,4,4,4-HEXAFLUOROBUTANE |
DE4305163A1 (en) | 1993-02-19 | 1994-08-25 | Bayer Ag | Process for the preparation of hexafluorobutene |
US5494601A (en) | 1993-04-01 | 1996-02-27 | Minnesota Mining And Manufacturing Company | Azeotropic compositions |
US5578137A (en) * | 1993-08-31 | 1996-11-26 | E. I. Du Pont De Nemours And Company | Azeotropic or azeotrope-like compositions including 1,1,1,2,3,4,4,5,5,5-decafluoropentane |
US5977271A (en) | 1994-09-02 | 1999-11-02 | The Dow Chemical Company | Process for preparing thermoset interpolymers and foams |
FR2731436B1 (en) | 1995-03-09 | 1997-04-30 | Atochem Elf Sa | USE OF HYDROFLUOROALCENES AS CLEANING AGENTS, AND COMPOSITIONS FOR USE THEREOF |
US5674621A (en) * | 1996-01-29 | 1997-10-07 | Eastman Kodak Company | Fuser members with an outermost layer of a fluorinated diamond like carbon |
US5900185A (en) | 1996-09-27 | 1999-05-04 | University Of New Mexico | Tropodegradable bromine-containing halocarbon additives to decrease flammability of refrigerants, foam blowing agents, solvents, aerosol propellants, and sterilants |
JP4315474B2 (en) | 1997-06-11 | 2009-08-19 | ダウ グローバル テクノロジーズ インコーポレーテッド | Absorbent extruded thermoplastic foam |
TR199902970T2 (en) | 1997-06-13 | 2000-05-22 | Huntsman Ici Chemicals Llc | Isocyanate compositions for foamed polyurethane foams. |
US5908822A (en) | 1997-10-28 | 1999-06-01 | E. I. Du Pont De Nemours And Company | Compositions and processes for drying substrates |
US6327866B1 (en) * | 1998-12-30 | 2001-12-11 | Praxair Technology, Inc. | Food freezing method using a multicomponent refrigerant |
US6610250B1 (en) | 1999-08-23 | 2003-08-26 | 3M Innovative Properties Company | Apparatus using halogenated organic fluids for heat transfer in low temperature processes requiring sterilization and methods therefor |
ATE307161T1 (en) | 2000-10-24 | 2005-11-15 | Dow Global Technologies Inc | PRODUCTION PROCESS FOR MULTI-MODAL THERMOPLASTIC POLYMER FOAM |
DE10055084A1 (en) | 2000-11-07 | 2002-06-13 | Basf Ag | Flexible, open-celled, microcellular polymer foams |
US6991744B2 (en) * | 2000-12-08 | 2006-01-31 | E. I. Du Pont De Nemours And Company | Refrigerant compositions containing a compatibilizer |
US6524496B2 (en) * | 2001-03-21 | 2003-02-25 | Honeywell International Inc. | Azeotrope-like composition of 1,1,1,3,3-pentafluoropropane and 1-chloro-1,1,3,3,3-pentafluoropropane |
US7279451B2 (en) | 2002-10-25 | 2007-10-09 | Honeywell International Inc. | Compositions containing fluorine substituted olefins |
ATE556124T1 (en) | 2002-10-25 | 2012-05-15 | Honeywell Int Inc | COMPOSITIONS CONTAINING FLUOROUS SUBSTITUTED OLEFINS |
US7161049B2 (en) * | 2002-12-13 | 2007-01-09 | E. I. Du Pont De Nemours And Company | Process for purifying hydrofluoropropanes |
EP1572753B1 (en) * | 2002-12-20 | 2012-06-13 | ExxonMobil Chemical Patents Inc. | Polymerization processes |
US20040248756A1 (en) * | 2003-06-04 | 2004-12-09 | Honeywell International, Inc. | Pentafluorobutane-based compositions |
US6969701B2 (en) | 2004-04-16 | 2005-11-29 | Honeywell International Inc. | Azeotrope-like compositions of tetrafluoropropene and trifluoroiodomethane |
EP1740189B1 (en) | 2004-04-19 | 2012-06-13 | Centre National De La Recherche Scientifique -Cnrs- | Lung surfactant supplements |
US7198728B2 (en) * | 2004-06-29 | 2007-04-03 | E.I. Du Pont De Nemours And Company | 1-ethoxy-1,1,2,2,3,3,4,4,4,-nonafluorobutane refrigerant compositions comprising a hydrocarbon and uses thereof |
WO2006094304A2 (en) * | 2005-03-04 | 2006-09-08 | E.I. Dupont De Nemours And Company | Refrigeration/air-conditioning apparatus powered by an engine exhaust gas driven turbine |
CN103462894A (en) | 2005-03-16 | 2013-12-25 | 霍尼韦尔国际公司 | Medicament delivery formulations, devices and methods |
US20060245944A1 (en) * | 2005-03-21 | 2006-11-02 | Leck Thomas J | Cooling apparatus powered by a ratioed gear drive assembly |
US20060266975A1 (en) * | 2005-05-27 | 2006-11-30 | Nappa Mario J | Compositions comprising 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene |
US20070077488A1 (en) | 2005-10-04 | 2007-04-05 | Kaimin Chen | Power capability of a cathode |
US7708903B2 (en) | 2005-11-01 | 2010-05-04 | E.I. Du Pont De Nemours And Company | Compositions comprising fluoroolefins and uses thereof |
PL1951838T3 (en) * | 2005-11-01 | 2013-12-31 | Du Pont | Compositions comprising fluoroolefins and uses thereof |
US20070098646A1 (en) | 2005-11-01 | 2007-05-03 | Nappa Mario J | Aerosol propellants comprising unsaturated fluorocarbons |
US20070100010A1 (en) | 2005-11-01 | 2007-05-03 | Creazzo Joseph A | Blowing agents for forming foam comprising unsaturated fluorocarbons |
MY160613A (en) | 2006-02-28 | 2017-03-15 | Du Pont | Azeotropic compositions comprising fluorinated compounds for cleaning applications |
CA2671048A1 (en) * | 2006-12-15 | 2008-06-26 | E.I. Dupont De Nemours And Company | Compositions comprising 1,2,3,3,3-pentafluoropropene with z- and e-isomer ratio optimized for refrigeration performance |
US8618339B2 (en) | 2007-04-26 | 2013-12-31 | E I Du Pont De Nemours And Company | High selectivity process to make dihydrofluoroalkenes |
ES2932622T3 (en) * | 2007-04-27 | 2023-01-23 | Chemours Co Fc Llc | Azeotropic and azeotrope-like compositions of Z-1,1,1,4,4,4-hexafluoro-2-butene |
CN101679841B (en) | 2007-06-12 | 2014-07-02 | 纳幕尔杜邦公司 | Azeotropic and azeotrope-like compositions of e-1,1,1,4,4,4-hexafluoro-2-butene |
AU2008279420A1 (en) | 2007-07-20 | 2009-01-29 | E. I. Du Pont De Nemours And Company | Compositions and use of trans-1,1,1,4,4,4-hexafluoro-2-butene foam-forming composition in the preparation of polyisocyanate-based foams |
JP2010534253A (en) | 2007-07-20 | 2010-11-04 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | Cis-1,1,1,4,4,4-hexafluoro-2-butene foam molding composition and use of the composition in the production of polyisocyanate-based foams |
CA2921867A1 (en) | 2007-09-06 | 2009-03-12 | E.I. Du Pont De Nemours And Company | Azeotropic and azeotrope-like compositions of e-1,1,1,4,4,5,5,5-octafluoro-2-pentene |
AU2008331468B2 (en) | 2007-11-29 | 2015-02-05 | The Chemours Company Fc, Llc. | Compositions and use of cis-1,1,1,4,4,4-hexafluoro-2-butene foam-forming composition in the preparation of polyisocyanate-based foams |
EP2222746B1 (en) | 2007-12-19 | 2015-10-28 | E. I. du Pont de Nemours and Company | Foam-forming compositions containing azeotropic or azeotrope-like mixture containing z-1,1,1,4,4,4-hexafluoro-2-butene and methyl formate and their uses in the preparation of polyisocyanate-based foams |
-
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- 2008-06-12 AU AU2008261695A patent/AU2008261695B2/en active Active
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-
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Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0558763A1 (en) * | 1991-09-25 | 1993-09-08 | Daikin Industries, Ltd. | Refrigerant and refrigerator |
JPH05179043A (en) * | 1991-11-18 | 1993-07-20 | Daikin Ind Ltd | Blowing agent comprising fluorobutene and production of plastic foam |
US20070007488A1 (en) * | 2003-10-27 | 2007-01-11 | Honeywell International, Inc. | Compositions containing fluorine substituted olefins |
US20070096051A1 (en) * | 2005-11-01 | 2007-05-03 | Nappa Mario J | Fire extinguishing and fire suppression compositions comprising unsaturated fluorocarbons |
US20070100011A1 (en) * | 2005-11-01 | 2007-05-03 | Creazzo Joseph A | Blowing agents for forming foam comprising unsaturated fluorocarbons |
US20070102021A1 (en) * | 2005-11-01 | 2007-05-10 | Nappa Mario J | Solvent compositions comprising unsaturated fluorinated hydrocarbons |
Non-Patent Citations (1)
Title |
---|
DATABASE WPI Week 199333, Derwent World Patents Index; AN 1993-261758, XP002494649 * |
Cited By (64)
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US8633339B2 (en) | 2005-11-01 | 2014-01-21 | E I Du Pont De Nemours And Company | Blowing agents for forming foam comprising unsaturated fluorocarbons |
US8558040B2 (en) | 2005-11-01 | 2013-10-15 | E I Du Pont De Nemours And Company | Methods for making foams using blowing agents comprising unsaturated fluorocarbons |
US7972524B2 (en) | 2007-04-27 | 2011-07-05 | E. I. Du Pont De Nemours And Company | Azeotropic and azeotrope-like compositions of Z-1,1,1,4,4,4-hexafluoro-2-butene |
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US8299137B2 (en) | 2007-11-29 | 2012-10-30 | E I Du Pont De Nemours And Company | Compositions and use of cis-1,1,1,4,4,4-hexafluoro-2-butene foam-forming composition in the preparation of polyisocyanate-based forms |
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US20110260093A1 (en) * | 2010-04-26 | 2011-10-27 | E.I. Du Pont De Nemours And Company | azeotrope-like compositions of e-1,1,1,4,4,4-hexafluoro-2-butene and 1-chloro-3,3,3-trifluoropropene |
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US9157018B2 (en) | 2010-11-25 | 2015-10-13 | Arkema France | Compositions of chloro-trifluoropropene and hexafluorobutene |
US10407603B2 (en) | 2010-11-25 | 2019-09-10 | Arkema France | Compositions of chloro-trifluoropropene and hexafluorobutene |
US9528039B2 (en) | 2010-11-25 | 2016-12-27 | Arkema France | Refrigerants containing (E)-1,1,1,4,4,4-hexafluorobut-2-ene |
US9528038B2 (en) | 2010-11-25 | 2016-12-27 | Arkema France | Compositions of chloro-trifluoropropene and hexafluorobutene |
WO2012069867A1 (en) | 2010-11-25 | 2012-05-31 | Arkema France | Compositions of chloro-trifluoropropene and hexafluorobutene |
US9267066B2 (en) | 2010-11-25 | 2016-02-23 | Arkema France | Refrigerants containing (E)-1,1,1,4,4,4-hexafluorobut-2-ene |
CN103228757B (en) * | 2010-11-25 | 2016-02-17 | 阿克马法国公司 | The composition of chlorine trifluoro propene and hexafluorobutene |
EP3543311A1 (en) | 2010-11-25 | 2019-09-25 | Arkema France | Use of compositions of chloro-trifluoropropene and hexafluorobutene |
CN103228757A (en) * | 2010-11-25 | 2013-07-31 | 阿克马法国公司 | Compositions of chloro-rifluoropropene and hexafluorobutene |
US9982178B2 (en) | 2010-11-25 | 2018-05-29 | Arkema France | Compositions of chloro-trifluoropropene and hexafluorobutene |
US10150901B2 (en) | 2010-12-03 | 2018-12-11 | Arkema France | Compositions containing 1,1,1,4,4,4-hexafluorobut-2-ene and 3,3,4,4,4-petrafluorobut-1-ene |
CN103370390A (en) * | 2011-01-19 | 2013-10-23 | 霍尼韦尔国际公司 | Azeotrope-like compositions of trans-1,1,1,4,4,4-hexafluoro-2-butene and water |
WO2012099844A3 (en) * | 2011-01-19 | 2012-10-18 | Honeywell International Inc. | Azeotrope-like compositions of trans-1,1,1,4,4,4-hexafluoro-2-butene and water |
US9359541B2 (en) | 2011-07-01 | 2016-06-07 | Arkema France | Compositions of 2,4,4,4-tetrafluorobut-1-ene and cis-1,1,1,4,4,4-hexafluorobut-2-ene |
US9145507B2 (en) * | 2011-07-01 | 2015-09-29 | Arkema France | Compositions of 2,4,4,4-tetrafluorobut-1-ene and cis-1,1,1,4,4,4-hexafluorobut-2-ene |
US20140083119A1 (en) * | 2011-07-01 | 2014-03-27 | Arkema France | Compositions of 2,4,4,4-tetrafluorobut-1-ene and cis-1,1,1,4,4,4-hexafluorobut-2-ene |
US9909045B2 (en) | 2012-04-04 | 2018-03-06 | Arkema France | Compositions based on 2,3,3,4,4,4-hexafluorobut-1-ene |
US9514959B2 (en) | 2012-10-30 | 2016-12-06 | American Air Liquide, Inc. | Fluorocarbon molecules for high aspect ratio oxide etch |
US10381240B2 (en) | 2012-10-30 | 2019-08-13 | American Air Liquide, Inc. | Fluorocarbon molecules for high aspect ratio oxide etch |
US11152223B2 (en) | 2012-10-30 | 2021-10-19 | American Air Liquide, Inc. | Fluorocarbon molecules for high aspect ratio oxide etch |
WO2018236477A3 (en) * | 2017-05-08 | 2019-04-11 | Honeywell International Inc. | Fire extinguishing compositions, systems and methods |
WO2019104055A1 (en) * | 2017-11-27 | 2019-05-31 | The Chemours Company Fc, Llc | Aerosol compositions |
GB2581732A (en) * | 2017-11-27 | 2020-08-26 | Chemours Co Fc Llc | Aerosol compositions |
WO2022261267A1 (en) | 2021-06-09 | 2022-12-15 | The Chemours Company Fc, Llc | Compositions comprising e-hfo-1336mzz and methyl formate and their use as expansion agents for thermoplastic foam |
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